3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine

Base Information

• Chemical Name: 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine
• CAS No.: 154925-95-8
• Molecular Formula: C21H39BrN2O5Si2
• Molecular Weight: 535.626
• Mol file: 154925-95-8.mol

Synonyms:3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine;5-BroMo-2'-deoxy-3',5'-bis-O-[(1,1-diMethylethyl)diMethylsilyl]-uridine

Chemical Property of 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine

Chemical Property:

• Melting Point: 142-144°C
• PSA: 82.81000
• Density: 1.212g/cm³
• LogP: 5.41110
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

99% ^*data from raw suppliers

3'',5''-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2''-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate in the preparation of cytidine derivatives

Technology Process of 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine

There total 1 articles about 3',5'-Bis-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-bromo-2'-deoxyuridine (59-14-3,723-73-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine (154925-95-8)

Guidance literature:

With pyridine; at 40 ℃; for 20h; Inert atmosphere;

DOI:10.1246/cl.2009.1046

Reference yield: 47.0%

2-aminoresorcinol (3163-15-3) + 3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine (154925-95-8) → C27H44BrN3O6Si2

Guidance literature:

3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine; With tetrachloromethane; triphenylphosphine; In dichloromethane; for 16h; Reflux;

2-aminoresorcinol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1039/c4sc00948g

Reference yield:

3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine (154925-95-8) → thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / n-BuLi, MeI / tetrahydrofuran; hexane / -78 °C

2: 1N HCl / methanol / 0.08 h / Heating

With hydrogenchloride; n-butyllithium; methyl iodide; In tetrahydrofuran; methanol; hexane;

DOI:10.1016/S0040-4020(01)80845-0

upstream raw materials:

5-bromo-2'-deoxyuridine

tert-butyldimethylsilyl chloride

Downstream raw materials:

thymidine

6-methyl-2'-deoxyuridine

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